Issue 24, 2011
From the journal:

Dalton Transactions

Cu(i) catalysed cyclopropanation with enantiopure scorpionate type ligands derived from (+)-camphor or (−)-menthone†

Tom Godau,‡a   Sascha M. Bleifuß,‡a   Astrid L. Müller,‡a   Thomas Roth,a   Susanne Hoffmann,a   Frank W. Heinemanna  and  Nicolai Burzlaff*a  

* Corresponding authors

a Inorganic Chemistry, Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nürnberg, Egerlandstr. 1, 91058 Erlangen, Germany
E-mail: Nicolai.Burzlaff@chemie.uni-erlangen.de
Fax: +49 9131-85-27387

Abstract

One-pot syntheses of three new enantiopure heteroscorpionate ligands derived from (+)-camphor or (−)-menthone are described. The ligands are obtained by reacting pyrazoles derived from (+)-camphor or (−)-menthone with sodium hydride and thionyl chloride. Subsequent reactions with pyridine and various aldehydes afford the tripod ligands in multi-gram amounts. Especially the menthopyrazole based ligand 6 showed encouraging ee values up to 69% in the Cu(I) catalysed enantioselective cyclopropanation of styrene with ethyl diazoacetate.

Graphical abstract: Cu(i) catalysed cyclopropanation with enantiopure scorpionate type ligands derived from (+)-camphor or (−)-menthone

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Article information

DOI
https://doi.org/10.1039/C1DT10032G
Article type
Paper
Submitted
09 Jan 2011
Accepted
12 Apr 2011
First published
16 May 2011

Dalton Trans., 2011,40, 6547-6554

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Cu(I) catalysed cyclopropanation with enantiopure scorpionate type ligands derived from (+)-camphor or (−)-menthone

T. Godau, S. M. Bleifuß, A. L. Müller, T. Roth, S. Hoffmann, F. W. Heinemann and N. Burzlaff, Dalton Trans., 2011, 40, 6547 DOI: 10.1039/C1DT10032G

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